Senior Delivery Manager

Robots & Pencils

. Lead end-to-end delivery of complex, multi-phase engagements across scope, budget, timeline, and quality .

Posted 10/6/2026full-timeRemote • CanadaSenior💰 CA$160,000 - CA$200,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in leading complex software delivery projects with a focus on AI-enabled platforms and agile methodologies. Proven ability to manage distributed teams, establish delivery standards, and communicate effectively with stakeholders across technical and non-technical backgrounds.

Highest-signal resume keywords

Agile Delivery PracticesAI Tools UsageClient-Facing CommunicationDelivery Tooling ExperiencePMP Certification

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Software DeliveryTechnical Project ManagementAgile MethodologiesAI Development Life CycleMulti-Platform Digital SystemsDelivery Standards SettingObservabilityModel Risk ManagementEvaluation StrategyHuman-in-the-Loop Checkpoints

Soft Skills

Relationship ManagementCoachingStakeholder CommunicationTeam LeadershipRisk Management

Tools & Technologies

JiraConfluenceGitHubAzure DevOpsCI/CD Pipelines

Certifications & Qualifications

PMPScrum MasterSAFe Certification

Industry Keywords

Consumer ProductsRetailEducationEnergyFinancial ServicesHealthcareManufacturingAI Co-WorkerApplied-AI InitiativesEngagement Management

Tech Stack

Tools & technologies

AzureCloudPMP

About the role

Key responsibilities & impact

Lead end-to-end delivery of complex, multi-phase engagements across scope, budget, timeline, and quality
Facilitate sprint planning, backlog refinement, and delivery execution across cross-functional teams
Manage phased releases, production readiness, and transitions into operations and maintenance
Identify and manage dependencies, risks, scope changes, and escalations
Define, track, and report delivery KPIs to guide decisions and tradeoffs
Support QA and UAT efforts and ensure acceptance criteria are met
Use AI tools such as Claude for delivery planning, reporting, and stakeholder communications
Implement the AI Development Life Cycle across engagements
Establish AI-augmented delivery standards, metrics, and processes
Partner with AI product managers and engineers on observability, model risk, data readiness, evaluation strategy, infrastructure, and production readiness
Set definitions of done for probabilistic and AI-driven features, including evaluation thresholds, human-in-the-loop checkpoints, and post-launch monitoring
Coach delivery managers and coordinators on AI-native and agentic development processes
Serve as primary delivery contact for clients and lead stakeholder, roadmap, and delivery forums
Communicate progress, risks, and tradeoffs to executive and non-technical audiences
Identify expansion opportunities and translate delivery progress into business impact
Lead distributed onshore and offshore delivery teams
Coach junior delivery managers and contribute to development plans
Improve delivery practices, tools, and frameworks across engagements
Assess team strengths and gaps, flag staffing needs, and participate in executive interviews and hiring decisions

Requirements

What you’ll need

5+ years of experience in software delivery, technical project management, or engineering leadership
Strong understanding of agile delivery practices across complex, multi-team engagements, including Scrum, SAFe, or Kanban
Experience managing distributed teams across onshore and offshore locations
Proven ability to deliver complex, multi-platform digital systems in agile environments
Strong client-facing communication and relationship management skills
Experience with delivery tooling such as Jira, Confluence, GitHub, Azure DevOps, and CI/CD pipelines
Familiarity with cloud-native architectures and AI-enabled platforms
Demonstrable usage of AI tools to enhance delivery planning, reporting, and documentation, such as Claude
Track record leading at least one engagement where AI/ML or agentic capability was core to the solution, including model risk, evaluation, and client expectations
Ability to set delivery standards for AI-native work, including evaluation criteria, human-in-the-loop checkpoints, and monitoring, and coach other delivery managers
Track record leading a team through an agentic development/delivery process, including observability, success metrics, and status visibility
Comfortable setting standards for infrastructure, context management, and latency trade-offs in an agentic delivery pipeline
PMP, Scrum Master, SAFe, or equivalent certification preferred
Vertical depth in one or more of Consumer Products and Retail, Education, Energy, Financial Services, Healthcare, or Manufacturing is helpful
Experience delivering agentic, AI co-worker, or applied-AI initiatives in enterprise is helpful
Prior client-facing experience in engagement management, consulting, or account leadership is helpful

Benefits

Comp & perks

Paid time off
Medical insurance
Dental insurance
Vision insurance
401(k) for eligible employees
Background check conducted in accordance with local legislation
Equal employment opportunities